Diastereodivergent Access to Syn and Anti 3,4-Substituted β-Fluoropyrrolidines: Enhancing or Reversing Substrate Preference

Kasper Fjelbye; Mauro Marigo; Rasmus Prætorius Clausen; Karsten Juhl

doi:10.1021/acs.orglett.6b00293

Diastereodivergent Access to Syn and Anti 3,4-Substituted β-Fluoropyrrolidines: Enhancing or Reversing Substrate Preference

Kasper Fjelbye, Mauro Marigo, Rasmus Prætorius Clausen, Karsten Juhl

17 Citationer (Scopus)

Abstract

A practical diastereodivergent access to β-fluoropyrrolidines with two adjacent stereocenters has been demonstrated, by either enhancing or completely reversing the substrate control, in the diastereoselective fluorination of a series of diverse pyrrolidinyl carbaldehydes using organocatalysis. Furthermore, enamine catalysis has been successfully utilized for kinetic resolution, obtaining a fluorinated β-prolinol analogue with two adjacent tetrasubstituted chiral centers in 95% ee from a racemic substrate.

Originalsprog	Engelsk
Tidsskrift	Organic Letters
Vol/bind	18
Udgave nummer	5
Sider (fra-til)	1170-1173
Antal sider	4
ISSN	1523-7060
DOI	https://doi.org/10.1021/acs.orglett.6b00293
Status	Udgivet - 4 mar. 2016

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10.1021/acs.orglett.6b00293

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title = "Diastereodivergent Access to Syn and Anti 3,4-Substituted β-Fluoropyrrolidines: Enhancing or Reversing Substrate Preference",

abstract = "A practical diastereodivergent access to β-fluoropyrrolidines with two adjacent stereocenters has been demonstrated, by either enhancing or completely reversing the substrate control, in the diastereoselective fluorination of a series of diverse pyrrolidinyl carbaldehydes using organocatalysis. Furthermore, enamine catalysis has been successfully utilized for kinetic resolution, obtaining a fluorinated β-prolinol analogue with two adjacent tetrasubstituted chiral centers in 95% ee from a racemic substrate.",

author = "Kasper Fjelbye and Mauro Marigo and Clausen, {Rasmus Pr{\ae}torius} and Karsten Juhl",

year = "2016",

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doi = "10.1021/acs.orglett.6b00293",

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T1 - Diastereodivergent Access to Syn and Anti 3,4-Substituted β-Fluoropyrrolidines: Enhancing or Reversing Substrate Preference

AU - Fjelbye, Kasper

AU - Marigo, Mauro

AU - Clausen, Rasmus Prætorius

AU - Juhl, Karsten

PY - 2016/3/4

Y1 - 2016/3/4

N2 - A practical diastereodivergent access to β-fluoropyrrolidines with two adjacent stereocenters has been demonstrated, by either enhancing or completely reversing the substrate control, in the diastereoselective fluorination of a series of diverse pyrrolidinyl carbaldehydes using organocatalysis. Furthermore, enamine catalysis has been successfully utilized for kinetic resolution, obtaining a fluorinated β-prolinol analogue with two adjacent tetrasubstituted chiral centers in 95% ee from a racemic substrate.

AB - A practical diastereodivergent access to β-fluoropyrrolidines with two adjacent stereocenters has been demonstrated, by either enhancing or completely reversing the substrate control, in the diastereoselective fluorination of a series of diverse pyrrolidinyl carbaldehydes using organocatalysis. Furthermore, enamine catalysis has been successfully utilized for kinetic resolution, obtaining a fluorinated β-prolinol analogue with two adjacent tetrasubstituted chiral centers in 95% ee from a racemic substrate.

U2 - 10.1021/acs.orglett.6b00293

DO - 10.1021/acs.orglett.6b00293

M3 - Journal article

C2 - 26902535

SN - 1523-7060

VL - 18

SP - 1170

EP - 1173

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Diastereodivergent Access to Syn and Anti 3,4-Substituted β-Fluoropyrrolidines: Enhancing or Reversing Substrate Preference

Abstract

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